“Dating is a battlefield—and in Chasing Cupid, we’re laughing through the shrapnel.”
If Sex and the City had a Gen Z cousin raised on chaos, comedy, and curated Instagram feeds—it would be Chasing Cupid. Let’s be honest: in the age of dating apps, voice notes, soft launches, and ghosting as a sport, finding love is less a fairytale and more of a meme-worthy misadventure. And thank Cupid someone finally captured it with the heart, humor, and raw relatability that it deserves.
Created by Lauren Davidi and Hillary Lewis, Chasing Cupid is a comedic gem of a web series now streaming on YouTube that dives headfirst into the hot mess that is modern dating. And I mean that lovingly. This show is fast, funny, fearless, and painfully on point—especially for those of us who’ve swiped right on disaster more times than we’d like to admit.
So what exactly is Chasing Cupid? Think: ten short-but-satisfying episodes, each around 7–12 minutes long, packed with cringe, charm, and characters you’ll instantly fall for. Set against the backdrop of millennial and Gen Z dating culture, the show follows five distinct women as they navigate first-date faux pas, hookup horror stories, emotional spirals, and everything in between—with each other as their ride-or-die support system.
But what makes Chasing Cupid different from the sea of “girl gang comedy” series? It doesn’t try to be polished or preachy. It embraces the imperfection, the awkwardness, and the chaos of real life—and that’s exactly where its magic lives.
Let me break it down for you.
Meet the Women Who Are Chasing Cupid
Each of the core five women is an archetype you’ve either been… or best-friended:
Maisey is what happens when unfiltered honesty meets unrelenting humor. She’s the lovable chaos goblin we all know (and lowkey are). She’ll show up to brunch in dog fur and leave with three new dating stories and a Venmo request. Her relationship status? “Let’s just see how it goes—probably nowhere.” Maisey’s energy is pure comic gold and her heart, despite the deflections, is big.
Cece is the drama. In the best way. Picture this: a couture tornado with a flair for texting her ex at 2 a.m. mid-margarita meltdown. She lives for the thrill, the chaos, and the impulsive decision-making that leads to hilarious regret. Cece is an entire plot twist in a red lip and stilettos.
Sofia is aspirational chaos. She’s boujee, bold, and allergic to anything under five stars. She lives at the intersection of high-maintenance and high charm, and I loved her instantly. Sofia’s growth throughout the series—from checklist dating to surprise vulnerability—adds depth to her designer-draped persona.
Apple Moon might have the most unforgettable name, but it’s her unapologetic self-love that steals the show. She’s every girl who’s ever been told she’s “too much” and decided to be even more. Watching Apple Moon lean into deeper connections while maintaining her fiery individuality? Chef’s kiss.
Piper is the hoodie-wearing, guitar-strumming girl with a soft spot for men who say things like “I don’t believe in labels.” She’s chill, grounded, and the glue of the group. If everyone else is spinning out, Piper’s the friend showing up with snacks and sage advice—while still making questionable choices of her own.
Together, this cast forms a friendship dynamic that is as fierce as it is funny. They roast each other, support each other, and navigate the minefield of dating while being fully themselves. And that authenticity? That’s what makes this series feel like a warm, chaotic hug.
The Humor Hits Different
Let’s talk tone. Chasing Cupid isn’t just funny—it’s smart funny. It’s observational, sometimes absurd, and often based on real dating experiences we’ve all survived.
Think improv-style confessionals. Think inner monologues that call out your exact thoughts mid-date. Think plot twists that actually catch you off guard because the writers trust the audience to keep up.
You’ll find yourself laughing out loud at lines like:
“His Hinge profile said ‘emotionally available,’ but so did my last pair of jeans—and those ripped too.”
“She said she wasn’t looking for anything serious, but then she Venmo-requested me for brunch… six months later.”
The series doesn’t try too hard to be trendy. It just is. It captures the way real people talk, spiral, flirt, and fight their way through situationships with shocking accuracy. The improv moments feel loose and fresh, allowing each actor to bring their own flair and nuance to their role. You can tell this cast isn’t just reading lines—they’re embodying their characters.
Visually and Emotionally Engaging
For a short-form YouTube series, the production value is on point. The lighting is warm and intimate, the pacing is fast but never frantic, and the scene transitions are clever enough to keep you hooked from one mini-meltdown to the next.
But what really grounds the show is its emotional depth. For every ridiculous date gone wrong, there’s a moment of raw vulnerability—those little quiet pauses where the laughter softens and we see the fears behind the filters.
Sofia questioning her traditional expectations. Cece dealing with the fallout of one too many impulsive decisions. Apple Moon realizing that confidence doesn’t mean closing yourself off. The show never wallows in emotion—but it doesn’t shy away from it either. That balance is rare and refreshing.
Why Chasing Cupid Matters Right Now
We are living in a time when dating culture has become increasingly gamified, curated, and frankly… exhausting. Chasing Cupid holds up a mirror to that reality—but with humor, hope, and heart. It reminds us that dating isn’t just about finding “the one.” It’s about discovering more of yourself through the missteps, the maybes, and the messy in-betweens.
It’s about having friends who know exactly how to hype you up when your situationship turns into a ghost town. It’s about laughing through the pain, screenshotting the receipts, and healing through shared chaos.
This series doesn’t lecture or moralize—it validates. It uplifts. And it absolutely entertains.
Chasing Cupid is the type of show you want to send to your group chat with the message: “This is literally us.” It’s low-commitment but high reward. It’s short, sweet, and brimming with bite-sized brilliance. You can binge it in one night and still feel like you’ve gone on an emotional journey—with friends, flings, and everything in between.
And the best part? It’s just getting started. With creators like Lauren Davidi and Hillary Lewis behind the scenes, there’s no doubt that Chasing Cupid will only grow in heart, hilarity, and relevance. The writing is sharp. The acting is authentic. And the series knows exactly who it’s speaking to—women who are tired of pretending dating is glamorous and would rather laugh through the mayhem instead.
So grab your oat milk latte, your emotional support water bottle, and settle in for a binge-worthy adventure that’s equal parts cringe, charm, and catharsis.
Because let’s face it: Cupid might be a mess—but so are we. And it’s about time someone made a show that gets it.
Where to Watch:
Catch Chasing Cupid on YouTube here: Watch the Pilot
New episodes drop weekly. Trust me, you’ll be waiting for the next one.
Follow the Chaos (and the love):
Instagram: @ChasingCupidSeries
TikTok: @ChasingCupidSeries
Words by Elle Taylor
